N-(1-azido-2,2,2-trihaloethyl)azides and carbamates as nematocides

ABSTRACT

AZIDES OF THE FORMULA   R-NH-CH(-N3)-C(-X)3   IN WHICH X IS CL OR BR AND R IS A CARBOXYACYL, SULFONYLACYL OR ALKOXYCARBONYL GROUP. THESE AZIDES ARE NEMATOCIDAL.

United States Patent O 3,752,890 N-(l-AZIDO-2,2,2-TRIHALOETHYL)AZIDES AND CARBAMATES AS NEMATOCIDES Malcolm S. Singer, Richmond, Calif., assignor to Chevron Research Company, San Francisco, Calif.

No Drawing. Original application Jan. 7, 1969, Ser. No. 789,595, now Patent No. 3,636,062. Divided and this application June 28, 1971, Ser. No. 163,522

Int. Cl. A01n 9/20 US. Cl. 424-226 10 Claims ABSTRACT OF THE DISCLOSURE Azides of the formula in which X is C1 or Br and R is a carboxyacyl, sulfonylacyl or alkoxycarbonyl group. These azides are nematocidal.

CROSS REFERENCE TO RELATED APPLICATIONS This application is a division of copending application Ser. No. 789,595, filed Jan. 7, 1969 now US. Pat. No. 3,636,062.

FIELD OF INVENTION This invention concerns N-(1-azido-2,2,2-trihaloethyl) amides and carbamates and their use as nematocides.

INVENTION DESCRIPTION The novel azides of this invention are carbamates, carboxamides and sulfonamides. These azides are of the formula Na R-NH-dH-OX:

wherein X is halogen of atomic number 17 to 35 and R is ELL wherein Z is a chalcogen atom of atomic number 8 to 16 and R is hydrogen, nonarylhydrocarbyl of 1 to 10 carbon atoms which is free of acetylenic unsaturation, nonarylhalohydrocarbyl which is free of acetylenic unsaturation and of 1 to 10 carbon atoms and 1 to 3 halogen atoms of atomic number 17 to 35, monocarbocyclicaryl of 6 to 15 carbon atoms, the benzene nucleus of said'monocarbocyclicaryl radical being substituted with to 3 alkoxy groups of 1 to 3 carbon atoms, each, halogens of atomic number 17 to 35 or nitro groups, alkoxy of 1 to 6 carbon atoms, henylthioalkyl in which the alkyl is of 1 to 3 carbon atoms and the phenyl is substituted with 0 to 2 halogen atoms of atomic number 17 to 35, phenylsulfonylalkyl in which the alkyl is of 1 to 3 carbon atoms and the phenyl is substituted with 0 to 2 halogen atoms of atomic number 17 to 35, or a S-membered heterocyclic radical of 4 nuclear carbon atoms, one of which is bound to the carbonyl radical of (a), and a single chalcogen heteroatom of atomic number 8 to 16, or

wherein R is a nonarylhydrocarbyl radical of 1 to 6 carbon atoms which is free of acetylenic unsaturation and is substituted with 0 to 2 halogen atoms of atomic number 17 to 35 or a monocarbocyclicaryl radical of 6 to 10 carbon atoms in which the benzene nucleus is substituted with 0 to 2 halogens of atomic number 17 "ice to 35, nitro groups or methoxy groups. Halogens of atomic number 17 to 35 are chlorine and bromine. Chalcogen atoms of atomic number 8 to 16 are oxygen and sulfur. The term nonaryl as used herein refers to radicals in which a benzene nucleus is not present. Preferably X is chlorine and Z is oxygen in the above formulas.

Particularly preferred compounds represented by the above formula are those in which X is chlorine, Z is oxygen, R is hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 3 carbon atoms, monoalkenyl of 2 to 5 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, monocarbocyclicaryl of 6 to 10 carbon atoms in which the benzene nucleus is substituted with 0 to 3 chlorine atoms, nitro groups or alkoxy groups of 1 to 2 carbon atoms each, chloroalkyl of 1 to 6 carbon atoms and 1 to 3 chlorine atoms, phenylthiomethyl in which the phenyl group is substituted with 0 to 2 chlorine atoms or phenylsulfonylmethyl wherein the phenyl group is substituted with 0 to 2 chlorine atoms and R is alkyl of 1 to 6 carbon atoms or phenyl substituted with 0 to 2 chlorine atoms.

Hydrocarbyl radicals which R represents in the above formula include alkyl, alkenyl, cycloalkyl and cycloalkenyl radicals. Specific examples of such radicals are methyl, ethyl, isopropyl, butyl, hexyl, heptyl, nonyl, decyl, vinyl propenyl, butenyl, pentenyl, octenyl, decenyl, cyclopropyl, cyclobutyl, cyclohexyl, cyclooctyl, cyclohexenyl and cyclooctenyl. Corresponding halohydrocarbyl groups represented by R include chloromethyl, bromomethyl, 2,2-dichloroethyl, 3-bromo-2-chloropropyl, 2-bromoethyl, 5-chloro-2-pentenyl, 6-chlorohexyl, 9-bromodecyl, 4-bromocyclohexyl, 2,4,6-tribromocyclohexyl, 2 chlorocyclohexenyl and 3-chlorocyclobutyl.

Examples of monocarbocyclic aryl radicals which R may represent are phenyl, tolyl, xylyl, cumyl, p-butylphenyl, p-octylphenyl, 2,4-dibutylph'enyl, cinnamyl, benzyl, pmethoxyphenyl, 2-methoxy-4-tolyl, 2,4,6-tripropoxyphenyl, 2,4,6-trinitrophenyl, 3,5-dibromophenyl, 2-chloro-4- methoxyphenyl, 2-bromo-4-tolyl, 2-chloro-4-ethylphenyl, 2,4,6-tribromophenyl, 2,4-diethoxybenzyl, 2,4-dinitrophenyl, 2-chloro-5-nitrophenyl and 5-nitro-2-tolyl.

Alkoxy radicals which R may represent include methoxy, ethoxy, isopropoxy, butoxy, isopentoxy and hexoxy.

Heterocyclic radicals which R may represent include Z-furyl, 4-furyl, 5-nitro-2-furyl, 5-chloro-2-furyl, 4-bromo- 2-furyl, 3-thieny1, 5-nitro-2-thienyl, 4-chloro-2-thienyl, 5- bromo-3-thienyl and 2-thienyl.

Phenylthioalkyl groups represented by R are illustrated by phenylthiomethyl, phenylthiocthyl, phenylthioisopropyl, 4-chlorophenylthioethyl, 2-chlorophenylthiopropyl, 3,S-dibromophenylthioethyl, 2,4-dichlorophenylthiomethyl and 2-chl0ro-4-bromophenylthiopropyl.

Phenylsulfonylalkyl radicals represented by R include phenylsulfonylmethyl, phenylsulfonylethyl, phenysulfonylisopropyl, 4 chlorophenylsulfonylethyl, Z-chlorophenylsulfonylpropyl, 3,5 dibromophenylsulfonylethyl, 2,4 dichlorophenylsulfonylmethyl and 2 chloro 4- bromophenylsulfonylpropyl.

Nonarylhydrocarbyl radicals which R may represent include alkyl, alkenyl and cycloalkyl. Examples of such radicals are methyl, ethyl, propyl, amyl, hexyl, allyl, pentenyl, 2,2-dibromoethyl, chloroallyl, bromobutenyl, cyclopropyl, cyclobutyl, cyclohexyl, 4 chlorocyclohexyl, 2 bromocyclohexyl, 3,5 dichlorocyclohexyl, 3-bromocyclobutyl, chloromethyl, bromoethyl, 2,2 dichloropropyl and 6-chlorohexyl. Aryl radicals represented by R include benzyl, phenyl, tolyl, xylyl, cumyl, 2,4-dinitrophenyl, 3,5 dimethoxyphenyl, 4 chloro benzyl, Z-bromo- 4-tolyl, 2-methoxyphenyl, 4-chlorophenyl, 2-bromophenyl, 4-bromo-2-chlorophenyl, 3,5-dichlorophenyl and 2,4-di- 'bromophenyl.

Carboxamides represented by the above formula include N(1-azido-2,2,2-trichloroethyl)-2,4-dipropoxybenzamide,

N- l-azido-2,2,2-tribromoethyl) -cyclohexanecarboxamide,

N( 1-azido-2,2,2-tribromoethyl -formamide,

N( 1-azido-2-bromo-2,2-dichl oroethyl -thioformamide,

N( 1-azido-2,2,Z-trichloroethyl)-3-chlorobutanamide,

N( 1-azido-2,2-dibromo-2-chloroethyl) -hexanamide,

N- 1-azido-2-bromo-2,2-dichloroethyl) -4,5-dichlorohexanamide,

N( l-azido-2,2,2-trichloroethyl -2-bromoacetamide,

N( 1-azido-2,2,2-trichloroethyl -thiobenzamide,

N(1-azido-2,2,2-tribromoethyl)-thioacetamide,

N- 1-azido-2-bromo-2,Z-dichloroethyl) -34bromothiopropionamide,

N- 1-azido-2,2,2-trichloroethyl) -thiocyclo pro panecarboxamide,

N- 1-azido-2,2,Z-trichloroethyl) -4-ethoxybenzamide,

N(1-azido-2,2-dibromo-2-chloroethyl)-2-chloro-4-bromothiobenzamide,

N( 1-azido-2,2,2-trichloroethyl) -4-bromo-3 -nitrobenzamide,

N( 1-azido-2,2,2-tribromoethyl -furamide,

N( l-azido-2,2,2-trichloroethyl-octanamide,

N-( 1-azido-2,2,2-trichloroethyl -decanamide,

N( 1-azido-2-bromo-2,2-dichloroethyl) -4-chlorocyclohexanecarboxamide,

N( 1-azido-2, 2, 2-trichloroethyl -cinnamamide,

N( 1-azid0-2,2,2-tribromoethyl -4-bromocinnamamide,

N( 1-azide-2,2,2-trichloroethyl) -S-hexeneamide,

N( 1-azido-2,2-dibromo-2-chloroethyl) --chlorofuramide,

N- 1-azido-2,2,2-trichloroethyl -2-phenylacetamide,

N( l-azido-2,2,2-trichloroethyl) -3- (4-chlorophenyl) propionamide,

N( 1-azido-2,2,2-trichloroethyl) -2- (4-bromophenylsulfonyl) acetamide,

N( 1-azido-2,2-dibromo-2- chloroethyl -5-nitrofuramide,

N- 1-azido-2-bromo-2,2-dichloroethyl -3 2,4-dichlorophenylsulfonyl) thiopropionamide,

N- 1-azido-2,2,2-trichloroethyl) -2-phenylthio-thi0- acetamide,

N( 1-azido-2,2-dibromo-2-chloroethyl) -3- (3,5-dichlorophenylthio propionamide,

N( 1-azido-2,2,2-tritbromoethyl -4,- (6-bromo-2-chlorophenylthio butanamide,

N- 1-azide-2,2,2-trichloroethyl)-4-(3-bromophenylsulfonyl butanamide,

N( 1-azido-2,2,2-tribromoethyl) -4-phenylsulfonylthiobutanamide, and

N(1-azodi-2,2-dibromo-2-chloroethyl)-3,5-diethoxythiobenzamide.

Sulfonamides represented by the above formula include N( 1-azido-2,2,2-trichloroethyl) -4-bromobenzenesulfonamide,

N( 1-azido-2-bromo-2,2-dichloroethyl)-3,4-dich1orobenzenesulfonamide,

N- 1-azido-2,2,2-trichloroethyl) -3 ,5 -dimethoxybenzenesulfonamide,

N- 1-azido-2,2,2-trichloroethyl) -3 -nitrobenzenesulfonamide, and

N- 1-azido-2-bromo-2,2-dichloroethy1) -2-nitro-4-chlorobenzenesulfonamide,

N( l-azido-2,2,Z-trichloroethyl) -methanesulfonamide,

N( 1-azido-2,2,2-tribromoethyl) -ethanesulfonamide,

N- 1-azido-2,2,2-tribromoethyl)propenesulfonamide,

N( 1-azido-2-bromo-2,2-dichloroethyl hexanesulfonamide,

N( 1-azido-2,2,2-trichloroethyl -2,2-dichloroethanesulfonamide,

N( l-azido-2,2,Z-trichloroethyl -bromobutenesulfonamide,

N( 1-azido-2,2-dibromo-2- chloroethyl hexenesulfonamide,

N( 1-azido-2,2,2-trichloroethyl cyclohexanesulfonamide,

N( l-azido -2,2,2-tribromoethyl) cyclobutanesulfonamide,

N( 1-azido-2,2,2-trichloroethyl) -3,5-dibromocyclohexanesulfonamide,

N( 1-azido-2,2-dibromo-2-chloroethyl) -3-chlorocyclobutanesulfonamide,

N( l-azido-2,2,2-trichloroethyl) -4-chlorobutanesulfonamide, and

N( 1-azido-2,2,2-trichloroethyl -3-bromo-4-chloropentanesulfonamide.

Carbamates represented by the above formula include N( 1-azido-2-bromo-2,2-dichlor0ethyl)-isopropy1- canbamate,

N( l-azido-2,2,2-trichloroethyl) -butylthiocarbamate,

N-( 1-azido-2,2,2-trichloroethyl -hexylcarbamate,

N( l-azido-2,2,2-trichloroethyl) -methy1thiocarbamate,

and

N-(1-azido-2,2-dibromo-2-chloroethyl)ethylcarbamate.

The azides of this invention are prepared by reacting a corresponding N(l,2,2,2-tetrahaloethyl) amide with an alkali metal azide. This reaction proceeds according to the following equation:

wherein R and X are as defined previously and M is an alkali metal such as sodium, potassium and lithium. This reaction will normally be carried out in polar, aprotic solvents such as acetonitrile, dimethoxyethane, tetrahydrofuran, dimethylformamide and dimethylsulfoxide. Normally the N (1 chloro 2,2,2 trihaloethyl)amide will be dissolved in the solvent to a concentration of about 5 and 20% by weight and the solid alkali metal azide will be added with agitation. The temperature of this reaction will usually be in the range of ambient temperature up to about C. More usually it will be betwen about 20 C. and 60 C. Stoichiometric proportions of the reactants will normally be employed. The pressure used in the reaction is not critical. For convenience atmospheric or autogenous pressure may be used. The N(1-azido-2,2,Z-trihaloethyl) amide or carbamate product may be recovered from the reaction mixture by filtering out the alkali metal halide and stripping the solvent from the filtrate.

The organic starting materials for the above reaction may be prepared by the method of British Pat. No. 993, 051. In this procedure an amide or a carbamate is condensed with a trihaloacetaldehyde. The resulting hydroxy compound is further reacted with thionyl chloride to replace this hydroxyl group with a chlorine atom. The reaction is as follows:

wherein R and X are as defined previously.

EXAMPLES The following examples illustrate the azides of this invention and their preparation. Unless otherwise indicated, percentages are by weight.

Example 1 21.1 g. N(1,2,2,2-tetrachloroethyl)formamide was dis solved in 100 ml. of acetonitrile. 6.5 g. of sodium azide was heated slowly at ambient temperature with stirring. The mixture was stirred overnight, after which the reaction mixture was filtered. The acetonitrile was removed from the filtrate leaving an orange liquid residue. This residue was cooled in an ice bath and the sides of the vessel containing the residue were scratched. After 30 minutes of this treatment, about 11 g. of N-(1-azido-2,2,2- trichloroethyl) formamide precipitated. This compound melted at 42-54 C. Its elemental analysis was: Calculated (percent): CI, 48.97; N, 25.75. Found (percent): 5 Cl, 48.05; N, 25.50.

Example 2 8.7 g. of N-(1,2,2,2-tetrachloroethyl)-4-chlorobenzene- 6 TABLE II Nematocidal activ- Compound: ity--percent N-(l-azido 2,2,2 trichloroethyl) 3,5 dimethoxybenzamide 100 N-(l-azido 2,2,2 trichloroethyl)-3,4,5-trimethoxybenzamide 100 N-(1-azido-2,2,2-trichloroethyl)-pivalamide 100 N-(l azido-2,2,2-trichloroethyl)-cyclopropanesulfonamide was dissolved in about 50 ml. acetonitrile. To 10 b id 100 this solution 1.58 g. of sodium azide was added with 1- d 2,2,2- i )-2,2- 1 mixing. The combined mixture was stirred for one hour. propionamide 100 Reaction mixture was then filtrated and the solid was 1- 2,2,2 i -2. 1 1. washed with cold acetonitrile. The acetonitn'le was evapfenyla et id 35 orated from the filtrate leaving an oil residue. This residue N. 1- q,2,2- 1 1y i 100 solldlfied p n standmg overnight, g g N-(1-azido-2,2,Z-trichloroethyl)-furamide 100 az1do-2,2,2 trichloroethyl)-4-chlorobenzenesulfonamide. 1- id 2,2,2 i )-3- h1 This sulfonamide melted at 112116 C. Its element pionamide 99 analysis was: Calculated (percent): CI, 39.0; S, 8.80. 1. 2,2, -3,4. 1 Found (percent): Cl, 37.82;S 9.39. benzamide 93 Other azides of this invention were prepared using the N. 1 id 2 2 2 i hl h -4. 1 .3- general procedures described above. These az des a e nitrobenzamide 95 tabulated m Table I bel W- N-( l-azido 2,2,2 trichloroethyl)-2,4-dichlorobenzamide 97 UTILITY N-(l azido-2,2,2-trichloroethyl)-2-ch1orobenz- The azides of this invention exhibit excellent biological amlde 95 activity against nematodes. The nematocidal activity of Y representative azides of this invention are illustrated by phenvlsulfonyl acetamlde 100 testing them according to the following method. 232,2 trlchlofoethyl)-2'PhenY1S11l- A 0.38 ml. portion of a 3% acetone solution of the y q 100 test compound was diluted with 1 ml. acetone. The reaZldO 2,2,2 y sulting solution was homogeneously mixed with 20 cc. nitrobenzamide 93 of vermiculite. The treated vermiculite was then mixed N-(l azido-2,2,2-tr1ch1oroethyl)-d1chloroacethomogeneously with 750 g. of soil, dry weight basis, amide 100 which was severely infested with nematodes (mixed cul- N-(l azido-2,2,2-trichloroethyl)-2-chloroacetture of Meloidogyne iavanica and Meloidogyne incognz'ta) amide 100 This mixing gave a concentration of approximately 15 N-(l-azido 2,2,2 trichloroethyl)-2-(4-chloroparts of the test compound per million parts of soil. This phenylthio)-acetamide 96 treated soil was stored for 4 days at 65-75 F. It was N-(l-azido- 2,2,2 -trichloroethyl)-isopropylcarthen divided equally into 3 parts, each of which was put 40 bamate 100 into a separate pot and kept for another 3 days. A 3- N-(l-azido 2,2,2 trichloroethyl)-4-chlorobenweek old tomato (v. Bonny Best) seedling was then transzenesulfonamide 100 TABLE I Elemental analysis, percent Calculated Found Melting Compound point, 0. C1 8 N 0 Cl 8 N C N-(l-azido-2,2,2-trlchloroethyl)-3,5-dimethoxybenzamide 93-99 30.06 30.35 N-(1-azido2,2,2-trichloroethy1)-3,4,5-trimethoxybenzamide 125-127 27.8 27.65 N-(l-azid0-2,2,2-trichloroethyl)-pivalamido 53-57 38.8 38.80 N-(l-azido-2,2,2-trichloroethylg-cyclopropanecarboxamide 127-127 41.4 40. 75 N-(1-azido-2,2,2-trichloroethyl -2,2-dichloropropionamide 37-38 56.4 17.80 52. 35 16.70 N-(l-azido2,2,2-trichloroethyl)-2-pheny1srflfenylacetamide 87-89 31.4 31. N-(l-azido-2,2,2-trich1oroethyl)-a,orylnmido 54-57 41.4 41.20 N-(l-azido-2,2,2-trichloroethyl)-Iuramide 94-98 87.6 37.15 N-(1-azido-2,2,2-trichloroethyl)-3-chloro ropionamid 78-89 50.7 49.05 N-(l-azido-2,2,2-triehloroethyl)-3,4-dich orobenzamide-.. 127-129 49.0 47.60 N-(l-azido-2,2,2-trichloroethyl)-4-chloro-3-nitrobenzamide 135-127 38.05 36.85 N-(l-azido-2,2,2-triehl0roethyl)-2,4-dichlorobeuzamide 81-83 49.0 48.15 N-(l-aaide-2,2,2-trichloroethyl)-2-eh1or0benzamide 110-116 43.3 42.30 N-(l-azido-2,2,2-triehloroethyl)-2-(4-chlorophenylsult'onyl) aceta 120-123 35.0 7.88 33.95 8.10 N-(l-azldo-2,2,Z-trichloroethyl)-2-phenylsulfonylaeetamide Liquid 28. 63 .62 28.95 8.62 N-(l-azido-2,2,2-triehloroethyl)-dichloroacetamide 108-110 59.1 58.10 N-(1-azid0-2,2,2-trich1oroethyl)-2-chloroacetamide 71.5-72.5 53.4 21 05 18.02 52.36 21.00 17 90 N-(l-azido-2,2,2-trichloroethyl)-2-(4-ch1oropheny1thi0)acetarm e 74-76 37.98 8.58 37.85 8 N-(1-azid0-2,2,2-tlichloroethyl)-isopropylcarbamate 46. 5-485 38.65 20. 34 36.95 .75

planted into each pot and incubated for 13 days under greenhouse conditions. After this period they were removed and the soil was washed from their roots. The nematocidal eflfectiveness of the test compound was determined by observing each plant for signs of nematode invasion (number of galls formed, stunting, etc.).

The results of these tests, reported as the average of the 3 replicates on a 0 to 100 basis-0 indicating no effectiveness; 100 indicating complete eifectiveness-are reported in Table II.

As illustrated above, the azides of this invention may be used to control plant-parasitic nematodes by exposing them to a toxic amount of the azide. Thus, these azides will normally be applied to nematode-infested soil at dosages in the range of 3 to 40 lbs. per acre. They may be applied as liquid formulations by spraying or injection. They may also be applied as solid formulations containing carriers such as soil, sawdust, clay and the like. When used as a solid, these azides will usually be plowed into the soil to facilitate their contact with the nematodes. Following their application to the soil, the soil will be watered to disperse the azide below ground level.

The above-mentioned liquid formulations will comprise, one or more azides admixed with a suitable solvent or diluent. Such formulations may be solutions, dispersions or emulsions. These liquid compositions Will also usually contain a surfactant to facilitate the azides penetration into the soil and generally enhance its effectiveness.

Nematocidal formulations of these azides may also contain stabilizers, spreading agents, fillers, other compatible pesticides and the like.

I claim:

1. A method for controlling nematodes which comprises exposing said nematodes to a nematocidally elfective amount of a compound of the formula a RNH-HOXa wherein X is halogen of atomic number 17 to 35 and R 1s wherein Z is a chalcogen atom of atomic number 8 to 16 and R is hydrogen; nonarylhydrocarbyl of 1 to 10 carbon atoms from the group consisting of alkyl, alkenyl, cycloalkyl and cycloalkenyl; nonarylhalohydrocarbyl from the group consisting of alkyl, alkenyl, cycloalkyl and cycloalkenyl and of 1 to 10 carbon atoms and l to 3 halogen atoms of atomic number 17 to 35; monocarbocyclicaryl of 6 to 15 carbon atoms, the benzene nucleus of said monocarbocyclicaryl radical being substituted with to 3 alkoxy groups of 1 to 3 carbon atoms each, halogens of atomic number 17 to 35 or nitro groups; alkoxy of 1 to 6 carbon atoms; phenylthioalkyl in which the alkyl is of 1 to 3 carbon atoms and the phenyl is substituted with 0 to 2 halogen atoms of atomic number 17 to 35; or phenylsulfonylalkyl in which the alkyl is of 1 to 3 carbon atoms and the phenyl is substituted with 0 to 2 halogen atoms of atomic number 17 to 35.

2. The method of claim 1 wherein X is chlorine and Z is oxygen.

3. The method of claim 1 wherein R is hydrogen; alkyl of 1 to 6 carbon atoms; monoalkenyl of 2 to 5 carbon atoms; cycloalkyl of 3 to 6 carbon atoms, monocarbocyclic aryl of 6 to 10 carbon atoms in which the henzene nucleus is substituted with 0 to 3 chlorine atoms, nitro groups or alkoxy groups of l to 2 carbon atoms each; chloroalkyl of l to 6 carbon atoms and 1 to 3 chlorine atoms; alkoxy of l to 3 carbon atoms; phenylthiomethyl in which the phenyl group is substituted with 0 to 3 chlorine atoms; or phenylsulfonylmethyl wherein the phenyl group is substituted with 0 to 3 chlorine atoms.

4. The method of claim 1 wherein R is hydrogen, 4- chlorophenyl, 3,5 dimethoxyphenyl, 3,4,5 trimethoxyphenyl, t-butyl, cyclopropyl, 2,2-dichloroethyl, phenylthiomethyl, vinyl, 2-chloroethyl, 3,4-dichlorophenyl, 4 chloro-3-nitrophenyl, 2-chlorophenyl, 4-chlorophenylsulfonylmethyl, phenylsulfonylmethyl, 2-chloro-5-nitrophenyl, dichloromethyl, chloromethyl, 4-chlorophenylthiomethyl or isopropoxy.

5. The method of claim 1 wherein Z is oxygen, X is chlorine and R is hydrogen.

6. The method of claim 4 wherein Z is oxygen and X is chlorine.

7. A nematocidal composition comprising a solid carrier or solvent and a nematocidally elfective amount of a compound of the formula a RNHHCX:

wherein X is halogen of atomic number 17 to 35 and R is Z Il -4L wherein Z is a chalcogen atom of atomic number 8 to 16 and R is hydrogen; nonarylhydrocarbyl of 1 to 10 carbon atoms from the group consisting of alkyl, alkenyl, cycloalkyl and cycloalkenyl; nonarylhalohydrocarbyl from the group consisting of alkyl, alkenyl, cycloalkyl and cycloalkenyl and of 1 to 10 carbon atoms and 1 to 3 halogen atoms of atomic number 17 to 35; monocarbocyclicaryl of 6 to 15 carbon atoms, the benzene nucleus of said monocarbocyclicaryl radical being substituted with 0 to 3 alkoxy groups of 1 to 3 carbon atoms each, halogens of atomic number 17 to 35 or nitro groups; alkoxy of 1 to 6 carbon atoms; phenylthioalkyl in which the alkyl is of 1 to 3 carbon atoms and the phenyl is substituted with 0 to 2 halogen atoms of atomic number 17 to 35; or phenylsulfonylalkyl in which the alkyl is of 1 to 3 carbon atoms and the phenyl is substituted with 0 to 2 halogen atom of atomic number 17 to 35.

8. The composition of claim 7 wherein X is chlorine. and Z is oxygen.

9. The composition of claim 7 wherein R is hydrogen, 4-chlorophenyl, 3,5-dimethoxyphenyl, 3,4,5-trimethoxyphenyl, t-butyl, cyclopropyl, 2,2-dichloroethyl, phenylthiomethyl, vinyl, 2-chloroethyl, 3,4-dichlorophenyl, 4-chloro- 3-nitrophenyl, 2-chlorophenyl, 4-chlorophenylsulfonylmethyl, phenylsulfonylmethyl, 2-chloro-5-nitrophenyl, dichloromethyl, chloromethyl, 4-chlorophenylthiomethyl or isopropoxy.

10. The composition of claim 7 wherein R is hydrogen, X is chlorine and Z is oxygen.

References Cited Weygand et al.: Chemische Berichte, vol. 99, pp. 1944, 1945 and 1955 (1966).

ALBERT T. MEYERS, Primary Examiner L. SCHENKMAN, Assistant Examiner 

